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Compound Detail

CHEMBL4581366

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CN[C@@H](C)C(=O)N[C@H](C(=O)N1CCC[C@H]1C(=O)N[C@@H]1CCc2c(OS(=O)(=O)F)cccc21)C1CCCCC1
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL4581366
Phase Preclinical
Structure Type MOL
InChI Key YVERFLKIJOIKPE-HXGJMTJLSA-N
4
Targets
15
Activities
2
Assay Types
3
PK Parameters
12
Publications
0
Known Names

Molecular Properties

552.7
MW (Da)
2.05
ALogP
7
HBA
3
HBD
133.9
PSA (Ų)
0.40
QED
1
Ro5 Violations
9
Rot. Bonds

Drug Information

Molecule Type Unknown
Availability Unknown
Chirality Unknown

Flags

First in Class Prodrug

Extended Properties

Molecular Formula C26H37FN4O6S
MW 552.67
Aromatic Rings 1
Heavy Atoms 38
NP-Likeness -0.41

Activity Summary

IC50 12 meas. best 8.05
EC50 3 meas. best 7.36

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Baculoviral IAP repeat-containing protein 3
CHEMBL5335
 IC50 8.05 7.8325 9.0 4
E3 ubiquitin-protein ligase XIAP
CHEMBL4198
 IC50 7.92 7.6575 12.0 4
Baculoviral IAP repeat-containing protein 2
CHEMBL5462
 IC50 7.85 7.745 14.0 4
MDA-MB-231
CHEMBL400
 EC50 7.36 7.2 44.0 3

Pharmacokinetic Data

Parameter Value Units Species
F 36.0 % Mus musculus
F 35.0 % Mus musculus
T1/2 2.0 hr Mus musculus

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Baculoviral IAP repeat-containing protein 3 IC50 = 9.0 nM 8.05 Inhibition of N-terminal 6x-His-tagged recombinant human cIAP2-BIR3 (244 to 349 ... 31550155
Baculoviral IAP repeat-containing protein 3 IC50 = 9.0 nM 8.05 Displacement of AVPI-biotin from cIAP2 BIR3 domain (unknown origin) incubated fo... 37262387
E3 ubiquitin-protein ligase XIAP IC50 = 12.0 nM 7.92 Inhibition of N-terminal His-tagged human XIAP-BIR3 (253 to 347 residues) expres... 31550155
E3 ubiquitin-protein ligase XIAP IC50 = 12.0 nM 7.92 Displacement of AVPI-biotin from human XIAP BIR3 domain (253 to 347 residues) ex... 37262387
Baculoviral IAP repeat-containing protein 2 IC50 = 14.0 nM 7.85 Inhibition of N-terminal 6x-His-tagged recombinant human cIAP1-BIR3 (258 to 363 ... 31550155
Baculoviral IAP repeat-containing protein 2 IC50 = 14.0 nM 7.85 Displacement of AVPI-biotin from cIAP1 BIR3 domain (unknown origin) incubated fo... 37262387
Baculoviral IAP repeat-containing protein 2 IC50 = 21.0 nM 7.68 Displacement of AVPI-biotin from cIAP1 BIR3 domain (unknown origin) preincubated... 37262387
Baculoviral IAP repeat-containing protein 3 IC50 = 21.0 nM 7.68 Displacement of AVPI-biotin from cIAP2 BIR3 domain (unknown origin) preincubated... 37262387
Baculoviral IAP repeat-containing protein 2 IC50 = 25.0 nM 7.6 Inhibition of N-terminal 6x-His-tagged recombinant human cIAP1-BIR3 (258 to 363 ... 31550155
Baculoviral IAP repeat-containing protein 3 IC50 = 28.0 nM 7.55 Inhibition of N-terminal 6x-His-tagged recombinant human cIAP2-BIR3 (244 to 349 ... 31550155
E3 ubiquitin-protein ligase XIAP IC50 = 38.0 nM 7.42 Inhibition of N-terminal His-tagged human XIAP-BIR3 (253 to 347 residues) expres... 31550155
E3 ubiquitin-protein ligase XIAP IC50 = 43.0 nM 7.37 Displacement of AVPI-biotin from human XIAP BIR3 domain (253 to 347 residues) ex... 37262387
MDA-MB-231 EC50 = 44.0 nM 7.36 Cytotoxicity in human MDA-MB-231 cells assessed as reduction in cell viability i... 37262387
MDA-MB-231 EC50 = 61.0 nM 7.21 Induction of apoptosis in human MDA-MB-231 cells 37262387
MDA-MB-231 EC50 = 94.2 nM 7.03 Cytotoxicity against human MDA-MB-231 cells cultured as 3D spheroids incubated f... 37262387

Literature References

PubMed DOI Target Context # Activities
31550155 10.1021/acs.jmedchem.9b01108 E3 ubiquitin-protein ligase XIAP 9
37262387 10.1021/acs.jmedchem.3c00467 E3 ubiquitin-protein ligase XIAP 9
31550155 10.1021/acs.jmedchem.9b01108 Baculoviral IAP repeat-containing protein 3 5
31550155 10.1021/acs.jmedchem.9b01108 Baculoviral IAP repeat-containing protein 2 5
31550155 10.1021/acs.jmedchem.9b01108 A549 3
31550155 10.1021/acs.jmedchem.9b01108 SK-MEL-28 3
37262387 10.1021/acs.jmedchem.3c00467 MDA-MB-231 3
31550155 10.1021/acs.jmedchem.9b01108 No relevant target 2
37262387 10.1021/acs.jmedchem.3c00467 Baculoviral IAP repeat-containing protein 2 2
37262387 10.1021/acs.jmedchem.3c00467 Baculoviral IAP repeat-containing protein 3 2
37262387 10.1021/acs.jmedchem.3c00467 ADMET 2
31550155 10.1021/acs.jmedchem.9b01108 ADMET 1

Data from ChEMBL 36 via Core Engine